IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Identification of caffeic acid as a major component of Moscatel wine protein sediment

Proteins play a significant role in the colloidal stability and clarity of white wines [1]. However, under conditions of high temperatures during storage or transportation, the proteins themselves can self-aggregate into light-dispersing particles causing the so-called protein haze [2]. Formation of these unattractive precipitates in bottled wine is a common defect of commercial wines, making them unacceptable for sale [3]. Previous studies identified the presence of phenolic compounds in the natural precipitate of white wine [4], contributing to the hypothesis that these compounds could be involved in the mechanism of protein haze formation.

Three Nebbiolo clone anthocyanin profile as affected by environmental conditions

Vitis vinifera ‘Nebbiolo’ cultivar is a 3’-subsituted anthocyanin prevalent wine variety. It is grown in North-West Italy for the production of high quality ageing wines. In the present work berry skin anthocyanin amounts and profiles of the clones CVT 308, CVT 423 and CVT 142 were studied in 2004 and in 2005 in four environmentally different locations of North-West Italy: Donnas (steep mountain area), Monforte (hilly area, with a pH of 8.1), Vezza (hilly area, with a pH of 8.2) and Lessona (plain area, with a pH of 4.8).

Towards a better understanding of the root system diversity and plasticityin young grafted vines using 2D imaging and 3D modelling tools

Three-dimensional functional-structural root architecture models, which decompose the root system architecture (RSA) into elementary developmental processes such as root emission, axial growth, branching patterns and tropism have become useful tools for (i) reconstructing in silico the spatial and temporal dynamics of root systems in a soil volume, (ii) analyzing their genotypic diversity and plasticity to the environment, and (iii) overcoming the bottleneck associated with their visualization and measurement in situ. Here, we present an original work on RSA phenotyping and modelling in grapevine. First, we developed 2D image-based analysis pipelines to quantify morphological and architectural traits in young grafts. Second, we parametrized and validated the 3D root model Archisimple on two rootstock genotypes (RGM, 1103P) grafted with V. vinifera Cabernet-Sauvignon and grown in different controlled conditions (rhizotrons, pots, tubes).

Proposta per un parco produttivo agrovitivinicolo dei “colli piacentini”

Le Dipartimento di Progettazione dell ‘Architettura del Politecnico di Milano et l’Istituto di Viticoltura della Facoltà d’Agraria di Piacenza dell’Università Cattolica del Sacra Cuore, ont elaboré une proposition pour réaliser, dans l’aire de colline de la province de Piacenza, un Parco Produttivo Agrovitivinicolo.

Climatic influences on Mencía grapevine phenology and grape composition for Amandi (Ribeira Sacra, Spain)

During the year 2009 we have studied the phenology and grape composition of Mencía cultivar in seven different situations (orientation and altitude) for Amandi subzone